Methyl Ethyl Ketone → HCID 19916766, compound

HRID 1756099Notes

Reaction equation

HRID 1756099 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.O.[NH2:13]N.[CH3:15][C:16]([CH2:18][CH3:19])=O>C(O)CC>[CH3:15][C:16]1[NH:13][C:2]2=[N:3][CH:4]=[C:5]([C:8]([F:11])([F:10])[F:9])[CH:6]=[C:7]2[C:18]=1[CH3:19]

Participants

5

Reactant 3

HCID 6569Methyl Ethyl KetoneHCID 24654Hydrazine hydrate (1:1)HCID 923422-Chloro-5-(trifluoromethyl)pyridine

Product 1

HCID 19916766HCID 19916766, compound

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

A mixture of 2-chloro-5-trifluoromethylpyridine (10 g 0.055 mol) and hydrazine mono hydrate (2,7 g, 0.055 mol) in 35 ml n-propanol was refluxed for 2 h and was then stirred 20 h at RT. To the solution was added 4,35 g (0.06 mol) methylethylketon and the mixture was refluxed for 30 min. After the solvent was removed under reduced pressure the residue was partitioned between methylene chloride and bicarbonate solution. The organic layer was dried over Na2SO4 and evaporated. The residue was solved in 80 ml diethylene glycol and refluxed for 5 h. The reaction mixture was poured into ice-water and extracted with methylene chloride. The organic layer was separated dried over Na2SO4 and evaporated. The residue was treated with warm petroleumether (60-80 ) wich was decantated and evaporated chromatography twice on silica gel with 1 methylene chloride/methanol 2 ethyl acetate, gave the desired product. (0,2 g 1.7% ).

Workup

  1. temperaturewas refluxed for 2 h
  2. temperaturethe mixture was refluxed for 30 min
  3. customAfter the solvent was removed under reduced pressure the residue
  4. customwas partitioned between methylene chloride and bicarbonate solution
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customevaporated
  7. temperaturerefluxed for 5 h
  8. additionThe reaction mixture was poured into ice-water
  9. extractionextracted with methylene chloride
  10. customThe organic layer was separated
  11. dry with materialdried over Na2SO4
  12. customevaporated
  13. additionThe residue was treated
  14. temperaturewith warm petroleumether (60-80 ) wich
  15. customevaporated chromatography twice on silica gel with 1 methylene chloride/methanol 2 ethyl acetate

Sources & evidence

ORD record
ord-56f2537d39c34de9959f04800389be22
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

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